23-year-old employee requests 37-year-old boss stops standing over her desk, has to comfort him when he starts crying: 'God forbid a girl tries to set a boundary'

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Ally Perry • Writer and Editor
Feb 20, 2026 9:00 PM EST

A good boss should be setting boundaries, not trying to break them.

When somebody assumes a managerial role in the workplace, that comes with a lot of responsibility. It means that they are directly responsible for the success and well-being of everyone who reports to them, no matter how they may feel about their fellow coworkers. Managing in a way that is fair, productive, and keeps everybody involved happy is a real skill that can be difficult to master. 

Above all else, it is important for a boss to act with professionalism. They are the people who are supposed to demonstrate the company values as guidance for all those who work with them. If time passes and they prove incapable of doing that, they start to run into problems. Not only may it show the higher-ups that they are ill-suited for the job, but it will also make them a pain to work with from an employee perspective. Nobody wants to come to work and feel like they have to take responsibility in a way that their manager should be doing. If it is not in the job description or the paycheck, it is not a fair way to act.

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  • a man in business attire sits on an office couch, running a hand through his hair
    via Vitaly Gariev

    The image does not depict the actual subjects of the story. Subjects are models.

  • A young female employee felt like she was being put in an unfair position when her boss would not stop spending too much time hovering over her desk. She had previously explained to him that this made her feel anxious, but he didn't seem to get the message.

    This time, when the man asked if there was something wrong, she told him that his behavior was making her uncomfortable and interfering with her work. This caused him to break down crying and ask for a hug, then tell her to take the rest of the day off. She was left confused and wondering if she had done something wrong.

  • Am I wrong for making my boss cry?

    My boss (37m) was hovering over me (23f) all morning. Not just checking in once or twice, but physically standing behind me while I was working.
    via Ok_Doughnut_301
  • After a while I started feeling really overwhelmed. For context, I've already had a conversation with him about this exact thing.
    via Ok_Doughnut_301
  • I've told him before that when he hovers, it makes me anxious and like I'm constantly doing something wrong.
    via Ok_Doughnut_301
  • I could tell he sensed the tension because he kept asking if something was wrong. Eventually I just said it again: the hovering is too much for me.
    via Ok_Doughnut_301
  • It makes me feel like I'm making mistakes even when I'm not. I wasn't yelling. I wasn't being dramatic.
    via Ok_Doughnut_301
  • I just repeated the boundary I've already set. And then he started crying. (god FORBID a girl try's to set a boundary) Like fully crying.
    via Ok_Doughnut_301
  • a woman's hands hold a pen and stick a Post-it note to a laptop on a crowded desk
    via Getty Images (Unsplash+)

    The image does not depict the actual subjects of the story. Subjects are models.

  • This is a grown man. (mind you i've known him less than a month) He started crying and asked me for a hug.
    via Ok_Doughnut_301
  • I was honestly caught off guard. It felt really uncomfortable and unexpected. He said he knows we both don't like negative energy and he doesn't want there to be tension between us.
    via Ok_Doughnut_301
  • I told him I don't want tension either, but I've already communicated this before and it's frustrating to have to keep repeating it.
    via Ok_Doughnut_301
  • He kept crying and then said something along the lines of, "If this isn't the right fit for you, that's okay.
    via Ok_Doughnut_301
  • And if it is, that's okay too." Then he told me to just take the rest of the day off.
    via Ok_Doughnut_301
  • So now I'm home, confused. I feel like I calmly communicated a boundary I've already expressed before, and somehow it turned into him crying and sending me home.
    via Ok_Doughnut_301
  • I genuinely don't know if I handled it wrong or if that reaction was just... a lot.
    via Ok_Doughnut_301
  • a young female employee sits at a desk, flipping through documents in a ring binder
    via Getty Images (Unsplash+)

    The image does not depict the actual subjects of the story. Subjects are models.

  • LabInner262 NTA Boss emotions are his to manage. Don't be concerned about it. But I have a suggestion. Next time he hovers, stop working, look at him and ask 'Do you need something?' Then go silent and wait for a response. Do not work until he leaves your area. Then resume working as if nothing had happened. In essence, this is the same way you teach a dog to not pull at a leash. When the dog pulls, stop. When the dog stops pulling, resume your walk. Eventually the dog learns that pulling is cou
    via LabInner262
  • Ok_Doughnut 301 Original Poster's Reply I'm not a confrontational person, and since we work in a customer facing environment, completely stopping what I'm doing would honestly make me more anxious because it would draw attention and feel like everyone is watching. I have thought about it though.
    via Ok_Doughnut_301
  • PDK112 NTA. He asked for a hug? No, that is inappropriate response. He is being manipulative and trying to get you to loosen your boundaries. Were there any witnesses? Have any coworkers indicated if this is normal?. Document what happened and send an email to HR. BCC your personal email address so you will have a copy. Perhaps frame it as you being concerned about his emotions and reactions, not as being threatened. Did he send you home with pay or did you have to clock out and lose money? If y
    via PDK112
  • superbound NTA. In case no one else said it, this guy is a CREEP. After you mentioned the hug, I'm worried he's not looking over your work so much as down your shirt. Go to HR.
    via superbound
  • Dry-Comfortable-3947 NTA I'd be walking right to HR.
    via Dry-Comfortable-3947
  • DJ_Mixalot NTA. You need to start documenting every incident with details and timestamps. You also should contact HR and let them know what happened - make sure you document that as well.
    via DJ_Mixalot
  • Batpark Of course you're NTA, this guy is weird
    via Batpark
  • LeftCommunication876 A hug? Hard pass. Time for a new job.
    via LeftCommunication876

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boss employee manager desk work workplace crying
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